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Synfacts 2010(7): 0794-0794  
DOI: 10.1055/s-0029-1220082
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of β-Substituted Tryptophans from Sulfonylindoles

Contributor(s): Mark Lautens, Jane Panteleev
B.-H. Zheng, C.-H. Ding, X.-L. Hou*, L.-X. Dai
Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
22 June 2010 (online)

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Significance

The authors report a synthesis of ;β-substituted tryptophans through a reaction of glycine with a sulfonylindole. Glycine is a common starting point to make a variety of unnatural amino acids (see Review below) and this work further exploits that strategy. Unnatural amino acids, such as these are present in a plethora of natural products and efficient access of these building blocks is usually noteworthy. The presented method is high-yielding and proceeds in good anti selectivity with good enantiocontrol.

Review: C. Nájera, J. M. Sansano Chem. Rev. 2007, 107, 4584-4671.